HALO depends on the altitude, but they have less wind resistance up there. Off the top of my head, I think they jump from 8,000 to 30,000 feet, depending on the aircraft.
I know that the fighter pilots can eject at those speeds, but they are encased in the seat and their flight suits (which aid in them resisting pressure and high Gs) and they are secured till they land. Even with all that protection, it can't feel good.
For the shuttle crew to use their chutes, they'd have to literally get to an opening, and jump out fully exposed. I've never jumped from anything like 200,000 feet, but I'd assume that they'd fall for quite a ways before the atmosphere would even be dense enough for the chute to work. They'd need oxygen, and probably some heat shielding, or they'd wouldn't make it. At 4000 mph, any significant air resistance could cause broken bones, fatal whiplash, or who knows what.
Catch 22, there. If the air resistance doesn't kill you, the fall to denser atmosphere will.